If you’ve ever played on a team before, you know that friendships often form on the baseball diamond, the soccer field or the tennis court. At first that friendship may form due to a shared passion for the sport but as time evolves, those friendships can deepen and create lasting almost family-like bonds. Such is the case with local men’s recreational softball team, the Wings. Several players have played together for twenty to thirty years or more.
Team manager, captain and coach Andy Benjamin was one of those long-term players and affectionately dubs himself the “great-grandfather” of the Wings as there are now several father-son duos playing on the team. Benjamin first started the team when they were known as the Misfits, then the Buffalo Wings and finally its current incarnation as the Wings. “We decided to name ourselves the Wings and drop the Buffalo because we are more than just an appetizer. You’ll still see our team logo has a buffalo with wings holding a bat,” he says with a laugh. Benjamin was the first to have his son Matt play alongside him on the Wings. Throughout the team’s history, there have been six father-son duos on the team. Many of those sons have joined after playing on the Horace Greeley baseball team and some have continued playing throughout college and even post college graduation. Currently, there are three father-son duos on the team roster. “We have a cornucopia of age with fathers, sons and even grandfathers playing,” notes Adam Kupperman, who first joined the team in 2008 and now plays alongside his son, Jared who graduated Horace Greeley this June and played for the baseball team.
Clearly there is something special about this team that makes the younger generation want to join the team and Benjamin credits that to the team’s chemistry and camaraderie. “It’s such a brotherhood, I can’t stress that enough.” Benjamin, who suffered a stroke a few years ago and no longer actively plays on the field says the team came to his aid when he was sick with hospital visits and emotional support. “When Andy got sick, we were all there for him. The team has the vibe of a family culture and that strong level of connection,” comments Kupperman.
Kupperman witnessed that unique bond first-hand when his daughter Kylie became sick again with medulloblastoma, a type of brain cancer. Kylie was first diagnosed with the disease as a four-year-old and had many grueling treatments throughout her life. The Horace Greeley graduate, was able to complete her freshman year at the University of Delaware when her tumor grew back. She passed away September 10, 2025 at the age of 19. The team was always there for the family from meal drops to helping out with anything. Kylie was an avid fan of the Wings and watched many games that her father played in. “Baseball is our first religion followed by Judaism,” jokes Kupperman, whose family has always been passionate about the sport.
Team member Jon Brolin first met Adam when they attended the University of Pennsylvania and were part of the same fraternity. Coincidentally, they both moved to Chappaqua and were placed on the same softball team. As a way to honor Kylie’s memory, Brolin created a pink baseball patch which now adorns the Wings uniforms emblazoned with “K13” on it. Pink was Kylie’s favorite color and “K” which is the eleventh letter of the alphabet signifies Kylie’s birthdate of November 13th. The number 13 holds special significance in the Kupperman family as Adam was born on March 13th. Kylie was also an ardent Taylor Swift fan and as any “Swifty” knows “13” is Taylor’s lucky number. Kupperman’s number on his uniform has always been 13.
Brolin explains that it is common practice in sports to wear a patch to honor someone important to the team who passed away for a season. “When I met up with Adam at Quaker Hill Tavern, (a favorite Wings hangout) to show him the patch, he got very emotional,” recalls Brolin. Echoing that sentiment, Kupperman says he got teary eyed. “It was heavy and an amazing gesture. It was incredibly thoughtful to create something in her honor and that he got the greenlight from the entire team. I got really choked up about the fact that it was the entire Wings team who stepped up because we are a family.”
Brolin says that the patch will be on their unforms in perpetuity, not just for one season. “When a new member joins the Wings, they will learn who Kylie was. In this way, she will always be part of our team.”
